Despite the fact that Dick Powell and Ruby Keeler are the stars in their seventh and final screen pairing, the key character here is Hugh Herbert. That unfortunately is Colleen's problem.
There are times when Hugh Herbert can be extremely funny, but a whole film really shouldn't be built around him. You can overdose on Hugh Herbert.
In the Road to Zanzibar one of the gags, but far from the whole film involved Crosby and Hope getting involved with eccentric millionaire Eric Blore. He goes around just giving the family fortune away and sells them a diamond mine for a nominal cost. Like Herbert in Colleen, Blore has his keepers. But the whole film isn't built around him.
In this film the family business is run by Dick Powell for Herbert who is his uncle and Herbert's sister Louise Fazenda. They've hired a keeper in Berton Churchill who breaks away from his usual stuffy banker type and here is the essentially decent, but eternally put upon keeper.
Herbert gets involved with a couple of sharpies, Jack Oakie and Joan Blondell who take advantage of this nut job to rake in some big bucks. Ruby Keeler is the bookkeeper at a dress shop that Herbert buys for Blondell and the Powell/Fazenda/Herbert family are now guarantors of all the debts owed and accruing.
Harry Warren and Al Dubin wrote some nice songs for the film that did not boast any hits at all. Dick Powell never even bothered to commercially record any of them. The finale had dancer Paul Draper cleverly worked in to partner with Ruby while Powell sang. It was always a problem with them as a team, Ruby's flat singing and the fact you'll notice Powell never danced in any of their films.
Colleen is pleasant enough entertainment, but the Powell/Keeler combination was definitely on the wane here.